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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1029270Generated: October 30, 2026

Isopropylbenzylamine → HCID 58168247, compound

https://huagongshe.com/reaction/1029270

Reaction equation

Participants

RoleNameHCIDCharge
ReactantIsopropylbenzylamineHCID 66024—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
ReactantSodium t-butoxideHCID 23676156—
Reactant9-chloro-5H-benzo[c][1,8]naphthyridin-6-oneHCID 58168298—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethyl SulfoxideHCID 679—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 58168247HCID 581682477%

Reaction Conditions

Temperature150 °C

Reaction Steps

6 (200 mg, 0.87 mmol), N-benzylpropan-2-amine (0.58 mL, 3.47 mmol), Pd(OAc)2 (8 mg, 0.03 mmol), X-Phos (33 mg, 0.07 mmol), and NaOtBu (250 mg, 2.6 mmol) were suspended in dioxane (3 mL), and stirred for 5 minutes at 150° C. via microwave. The reaction solution was diluted with DMSO and filtered. The crude product was purified directly via prep-LC-MS to provide 448 (21 mg, 7% yield) as a white powder. LC-MS (M+H=344, obsd.=344). 1H NMR (400 MHz, DMSO-D6) δ 11.45 (m, 1H), 8.53 (m, 1H), 8.38 (m, 1H), 8.00 (s, 1H), 7.49 (m, 1H), 7.32 (m, 5H), 7.18 (m, 1H), 7.00 (m, 1H), 4.66 (s, 2H), 1.25 (d, J=6.6, 6H), 0.84 (m, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735584B2
Source datasetuspto-grants-2014_05
ORD IDord-241e20053bec4d0d897cef55de500381
Source noteuspto-grants-2014_05